
Vacation rentals in Sag Harbor
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Top-rated vacation rentals in Sag Harbor
Guests agree: these stays are highly rated for location, cleanliness, and more.

Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Whaling Captain Pierson's Apartment TOO
Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Secluded Southampton Cottage w/Pool & Spa
*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Updated apartment in historic village home
Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Sag Harbor Village Cottage with Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Breezy Waterfront Home With private Dock
This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Charming Southampton Light filled Cottage
Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Artists Sag Harbor Village Retreat
This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

Light-filled Sag Harbor village gem
Midcentury style in the heart of Sag Harbor Historic district. Soaring 20-foot floor-to-ceiling windows and skylights throughout offer the ideal indoor-outdoor experience for enjoying all seasons. Featured in Home & Garden, the house is situated on sprawling grounds, one of the largest lots in Sag Harbor. In the winter, enjoy the Scandinavian sauna and lounge in front of the fireplace. Gunite pool open May 25 to Sept 3.

Cheerful East Hampton home with Pool
Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!
Popular amenities for Sag Harbor vacation rentals
Sag Harbor beach vacation rentals

Walk-To-The-Beach House In The Dunes

Savor Ocean Sunsets at a Soothing Beachfront Haven

Best View + Putting Green + Private Beach

Historic East Hampton Home - Private Beach Access

Private beach, fully updated house, on 2 acres.

Beautiful Waterview Condo on the North Fork of LI

Year Round Hamptons Waterfront

Waterfront Autumn Escape in Wine Country: 2BR
Other great vacation rentals in Sag Harbor

Beach Cottage | Steps to Water| Fireplace|Firepit
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Charming Cottage in Sag Harbor

Hamptons Designer Cottage w Pool by Wölffer Estate

The Perfect Summer Beach Home in Sag Harbor

Charming Village Cottage

1800 Historical EH Home, 1 Mile to Town!

Wake up to Stunning Views at a Serene Waterfront Haven
When is the best time to visit Sag Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 320 | € 320 | € 320 | € 384 | € 552 | € 637 | € 752 | € 829 | € 597 | € 422 | € 477 | € 320 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Sag Harbor?
Yes! Work meets play with ease at over 140 vacation rentals in Sag Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Sag Harbor?
Four-legged friends are welcome in Sag Harbor. Choose from more than 100 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Sag Harbor?
Experience the best of Sag Harbor with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Sag Harbor have wifi?
Absolutely! We offer over 200 house rentals with wifi in Sag Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there Sag Harbor house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 110 house rentals with pools in Sag Harbor, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Sag Harbor have a gym?
Absolutely! We offer over 40 house rentals with a gym in Sag Harbor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sag Harbor have a bbq area?
Absolutely! We offer over 100 house rentals with a bbq area in Sag Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Sag Harbor?
Sag Harbor has more than 180 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Sag Harbor

Total vacation rentals
Explore 270 vacation rentals in Sag Harbor

Nightly prices starting at
Sag Harbor vacation rentals start at € 77 per night before taxes and fees

Verified guest reviews
Over 7,730 verified reviews to help you choose

Family-friendly vacation rentals
210 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
120 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
260 of Sag Harbor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Beachfront, Gym, and BBQ grill across Sag Harbor rentals

4.9 Average rating
Sag Harbor stays are highly rated by guests—averaging 4.9 out of 5!
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